


FAILBOAT HOOKER STILES

by DomesticatedChaos



Category: Teen Wolf (TV)
Genre: Blow Jobs, Crack, Failboats, First Kiss, First Time, Happy Ending, M/M, Prostitute Stiles Stilinski, Prostitution, Ridiculous, Sheriff in the hospital, and Stiles just really really wants to get laid, people keep trying to save Stiles
Language: English
Status: Completed
Published: 2015-03-12
Updated: 2015-03-12
Packaged: 2018-03-17 13:24:53
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 7,039
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3530963
Author URL: https://archiveofourown.org/users/DomesticatedChaos/pseuds/DomesticatedChaos
Summary: <blockquote class="userstuff">
              <p>Stiles's dad is in the hospital so he decides to sell himself on the mean streets of San Francisco to pay for the overwhelming amount of debt he finds himself in. Should be pretty easy, right? Except everyone keeps trying to save him and take care of him and now Stiles just really, really, really wants to get laid.</p>
            </blockquote>





	FAILBOAT HOOKER STILES

**Author's Note:**

> Inspired by this [prompt](http://drunktuesdaze.tumblr.com/post/107366775859/sinsensory-drunktuesdaze-helenish-just-said).
> 
> There is literally no better fitting title than FAILBOAT HOOKER STILES. Believe me. M and I tried to find one and we couldn't.
> 
> I'd like to say this is the most ridiculous thing I've ever written, but it's not. It's not even the second most ridiculous. I am sensing a pattern, actually.
> 
> But look! Actual porn! :D

With his father in the hospital recovering from emergency open heart surgery, Stiles has no other choice but to go out into the streets to earn enough money to cover the cost of his home and food. And if he's really lucky, a little to set aside for the heaping mounds of medical bills piling up.

Scott wasn't so sure about the idea, but then again, Scott frequently has dumb ideas, so Stiles isn't sure Scott is the best opinion to consult on these matters. Besides, Stiles fucking loves to jerk off, so this is just like, the next level of sexuality, right? And he'll get paid for it.

(He cried the last time he opened up the electricity bill. He definitely needs money.)

He explores other avenues first. Okay, second, because to be honest, he really does think he’d be good at the sex thing if he ever gets the chance to try it. But he knows that his father will never approve of the idea of Stiles being a porn star (which WOW all the porn sites take like, a huge fucking percentage from amateur videos and unless Stiles gets four million hits he’s not going to make enough to cover _ramen_ never mind his internet bill) or a prostitute (without a pimp, Stiles might actually make bank).

He turns in eighteen different applications to various places, and all of them say that they’ll “call him” in that insipid voice that Stiles knows to mean “good fucking luck.” He’s not hopeful.

So it’s back to the prostitution. Besides, he really _does_ think he’d be good at it. And with Stiles being a virgin, he hopes that just makes it all the more appealing and lucrative. Because virginity is a niche market that people pay tons of money for.

So Stiles packs a bag and drives all the way down to San Fran one weekend, using pilfered change here and there to afford the gas to get there (but not for a return trip--he really needs to get paid), and scouts out a nice little corner for himself in the crappier parts of town. He changes in the Jeep--not like he can afford a hotel room--and emerges in a tight t-shirt and ripped-up jeans that have seen better days.

And he waits.

Twenty minutes later, a guy walks by, peering curiously at Stiles.

"What are you doing here, kid?" the man asks.

Stiles instantly perks up, then reminds himself he's trying to be all seductive and sexy and shit, and relaxes against the wall once more. "Nothing. I mean, not much. Just, you know... hanging around." His seduction techniques could use some work. He winces, hopefully more mentally than actually, and tries to put on his best smile.

The guy stares at him. Stiles is pretty sure he's scaring him off, and is just about to turn around to... do what, Stiles doesn't know, when the guy makes the face the people do when they see cute baby animals. He literally coos at Stiles. "Aww, c'mere kid. You hungry? I'll get you something to eat."

_Motherfucking finally. A customer._  Stiles nods happily, muttering something about him being so starved he could eat a horse. (Not that he would. He likes horses. Or at least, he thinks he would like horses. He hasn't actually ever been near a horse.)

The guy delicately places his hand in the small of Stiles's back and leads him down a few blocks to a nice looking diner, one of those vintage '50s looking ones with red vinyl seats and black and white tiled floors. Stiles smiles at the guy as he holds the door open for him, like a gentleman. _Maybe he'll tip well. This won't be a bad way to finally lose my v-card. And I'll get dinner out of it, too!_

They're seated in the back booth, and the guy tells Stiles to order whatever he wants. Stiles takes about two seconds to look at the menu. They have curly fries. He's definitely getting curly fries.

The waitress comes back, and they place their order. In fact, the guy orders Stiles extra food, like Stiles could eat three sandwiches and three orders of fries _and_  a milkshake _and_ spinach dip appetizer all in one sitting.

Okay, he probably could, but he was trying to be sexy and not like, bloated and passed out in a food coma.

They make small talk while they wait for the food. Stiles hopes the guy is going to eat some of it, because otherwise he's going to feel like a fucking pig.

"How long have you, you know, been out there?" the guy asks.

Stiles shrugs and slurps on his soda. "Not long." He doesn't want the guy to know that he's barely been a hooker for an hour. No, wait, the virgin innocent thing is supposed to be appealing, right? Stiles bats his eyelashes. "Actually, this is my first night."

"What about your parents?"

Stiles folds in on himself. He knows, intellectually, that a sob story will help to open up people's wallets, but still. "My dad's in the hospital. Heart surgery." He looks around the diner, momentarily wishing he was anywhere but here. "My mom is, um, dead." 

The guy makes a sound like a wounded bird, and reaches across the table to lay his hand on Stiles's. "Oh, baby."

The guy's hands are warm. Stiles just wants his food.

But with that bit of awkwardness over, the night actually passes sort of pleasantly. The guy--Frank--is pretty funny, and better yet, laughs at Stiles's dumb jokes. They talk about Star Wars. The food is really good--best curly fries Stiles has ever had, actually--and Frank gets the waitress to box of the remaining amounts of food "for later." Stiles is starting to think that Frank wants to take him back to his place, to, you know, complete the transaction, and maybe have a midnight snack to reinvigorate themselves for round two. Stiles is down with that idea. He likes the way Frank laughs and really? Frank is kind of sexy. Stiles is _totally_  okay with the idea of losing his v-card to Frank.

They're standing outside the restaurant, a bit awkwardly, Stiles with a plastic bag looped around his wrist containing two large Styrofoam containers of food and an extra Styrofoam soup bowl filled with potato salad (also super good. Damn, Stiles is coming back to this diner when he has, you know, actual money.).

Trying to be sexy, Stiles looks at Frank and asks, "So, do you have a room? Do you want to, you know, finish our date?"

Frank gives Stiles a look like he just announced his puppy died in some freak boating accident, and immediately envelopes Stiles into a warm and cuddly hug. When he releases Stiles, he pulls out his wallet and hands Stiles a hundred dollar bill. "Stay safe out there. Do you have a place to go? I think there's a halfway house around the corner, near 2nd." He hugs Stiles one more time, and walks away, looking back a couple of times fondly.

Stiles stands in the middle of the sidewalk, poleaxed, with $45 of food on his wrist and another $100 cash in his hand. And still firmly in possession of his v-card.

"Huh," he says to no one but himself.

\--

Even though he has plenty of money to refuel the Jeep and return to Beacon Hills, and food for the weekend (if he’s careful), his $100 isn't going to help him with the house payment and utilities, never mind the medical bills. So Stiles stashes the food in his Jeep and returns to his corner. It’s about 9:30 so he'll stay out until 2 or so then crash in his Jeep and reevaluate in the morning. 

An hour later, Stiles really wishes he'd thought to bring a jacket with him. By a little after 11, his teeth chatter so badly that he's pretty sure he's going to freeze to death. Which kind of the exact opposite he wants to have happen, so he heads back to his Jeep to see if maybe he left a sweatshirt or something in the back of it. It may not be sexy, but he won't be a little Stiles popsicle in the morning.

He's headfirst in the back of the jeep, ass sticking straight up in the cold, cruel air when he hears this hesitant "ahem" behind him. He startles badly, hitting his head on the doorframe (but, more importantly, clutching a windbreaker he had forgotten he even had).

There's a pair of guys looking at him. He holds the windbreaker to his chest. "Hey," he starts. "What's up, fellas?"

Great. They're probably muggers and Stiles is going to die a virgin hooker.

The guy on the right narrows his eyes at Stiles, like he's trying to figure out who he is. "What are you doing?"

Oh. Maybe they're not muggers. Maybe they're concerned citizens and think that Stiles just broke into the Jeep to steal stuff. Great, they'll probably call the cops, and just exactly how is Stiles going to explain to the officers that he's a 17-year-old virgin hooker trying to turn tricks, not break into cars? That'll go over _real_ well. 

Plus, they'd probably call his dad. So double not good.

"Just uh," Stiles tries to answer. "Just getting my jacket. It's pretty cold out here, you know?"

The guy nods--not that he looks cold. He's wearing a leather jacket that's probably worth more than Stiles's Jeep. That, and he also looks drunk, and drunkenness is a pretty good way to stay warm in Stiles's opinion.

"What are you doing outside?" the guy asks. His dark-haired friend nods, like this was also concerning him, although he stays silent.

Stiles struggles into his windbreaker. It is mildly helpful at cutting the chilly wind kicking up from over the bay. "Working."

"Working? At this time of night?" the blond says, but the silent dude on the left jabs him in the ribs with an elbow.

"He means working. The streets."

The other guy's eyes go wide. Stiles blinks at the pair. He wonders if they're going to pick him up or if he should try escaping back to his corner to wait out the night, like he planned. Two guys at once seems kind of daunting for his first time, but then again, it _is_ a frequent masturbatory fantasy of his, so why not? Plus he could probably charge them double. Because threesome.

"You, uh, looking for a good time?" That line sounds way better in Stiles's head. He cringes.

But the dudes just give him this look, like what Stiles said is the saddest thing they've ever heard. They have a quiet discussion (well, not that quiet--Stiles hears damn near everything they say) about what to do and maybe they should help the poor kid out and hey, I've got some clubbing money left and... "Yeah. Sounds good to us."

Stiles does a mental victory dance, complete with a shimmy and jazz hands. "Awesome. You got a place, or...?"

The guys nod. "Just down the road." The one on the right looks at the Jeep. "You wanna drive?"

Ah. Surprisingly good thinking coming from a drunk guy. Stiles is loathe to part with his Jeep—it’s his only means of escape. And plus, with him driving, there'll be no chance of them kidnapping him, right? Stiles nods quickly and turns to unlock the Jeep's doors. 

"Climb on in. Sorry about the mess."

It takes a few minutes rearranging, but he finally gets his two johns into his car and himself behind the wheel. (The dark haired guy’s name is Adam and the other is Steve. Stiles swallows a snort of laughter when he learns that. Adam and Steve? Oh my god.) He follows their instructions until they're turning into the driveway of a decent-looking hotel. Like, there's a lighted fountain by the entrance and everything.

"Guys, you sure about this? This place is swanky." Oh god, Stiles sees a bellhop with actual epaulettes. What the hell do these dudes expect Stiles to do to them if they're bringing him to a place like this?

Adam just waves Stiles off. "Yeah, this place is good. Don't worry about it." Steve just nods and grins and pats Stiles happily on the shoulder.

Steve pays and gets a key to the room. The elevator ride to the fifth floor is one of the most awkward in all of Stiles's life.

"So... What are you fellas into?" Stiles doesn't even know if he means in general or what they want to do to him. Either answer is fine by him. 

Steve just makes a cooing noise that Stiles is swiftly becoming acquainted with. Adam nudges him playfully in the shoulder. (Well, upper arm. Stiles has a good four inches on the guy.) The elevator doors open. Stiles sighs.

The pair sways to their paid hotel room, Stiles following helplessly behind. They let him into the room, where Stiles stands, a bit lost, in the center of the small foyer. Steve, for some insane reason, goes immediately into the bathroom while Adam turns on the television. "What do you wanna watch?"

Stiles blinks. "Um, porn?" He has no idea what Adam is asking.

Adam shrugs, as if porn is a normal every day topic for him. Then again, maybe he picks up underage hookers a lot, so it could be a normal everyday topic for him. "If that's what you're into. I was thinking of Pacific Rim myself."

Stiles nods. "Oh yeah. I love that movie."

They're getting settled on the bed, watching the opening scenes of the movie, when Steve finally comes out of the bathroom. He gives a little nod of satisfaction and Adam smirks. Stiles feels like this is some kind of inside joke that he's not even sure he wants to be privy to.

Oh, who the hell is he kidding. "What?"

It's Adam who answers. "Steve approves of the shower."

Steve flops onto the bed. "Good water pressure; it heated up quickly. And it has one of those curved shower curtain rods so it makes everything roomier."

Stiles stares at the two of them. Great. He's been picked up by whack jobs.

They watch a decent amount of the movie together, Steve lounging like a cat behind Adam and Stiles, Adam leaning heavily into Stiles's shoulder and occasionally petting his hair, and Stiles becoming more and more confused by the second. It's all very cuddly, but not very sexy, and definitely not in a "I'm going to pay an underage hooker to bang my brains out" kind of way. In fact, any more of the petting and Stiles may fall asleep.

Mako Mori has just beaten the crap out of Raleigh when Steve nudges Adam. "We should go."

Adam sits up, yawns, and stretches. "Yeah." He gets off the bed and turns to Stiles. Behind them, Steve is doing the same. "You're going to be okay here, right? The room is paid for through the night. Check out is at noon. Just leave the key at the desk downstairs."

Stiles blinks at them. "Um?"

Steve nods like Stiles nonsensically mumbling made sense. "Oh yeah. We should definitely--"

The pair pulls out their wallets and pool together a pile of cash, which they hand solemnly out to Stiles. Stiles grabs it. On the top of the pile is a business card with Steve's name on it.

"Um," Stiles says again.

Steve leans over and hugs Stiles. "Call if you need anything, okay?"

Before Stiles can respond, Steve lets go and Adam hugs him, nuzzling the side of his face fondly. Stiles has stubble burn by the time Adam is done. "Be safe."

Stiles doesn't know what to do other than nod. So he nods.

The pair waltzes out of the door, clicking it shut with sound of finality, leaving Stiles alone on the cushy bed and the sounds of Jaegers beating the tar out of Kaiju on the television screen. He looks down at the wad of cash in his hand, and counts it. 

$235. 

Holy fucking shit.

Stiles flops on the bed, completely confused and flabbergasted and this bizarre turn of events. He also realizes that he hasn't been laid yet. Two successful tricks in one night, and Stiles is still a virgin.

He doesn't even fucking know anymore.

\--

As much as Stiles is kind of disturbed by how easy it was to make about $350 (plus free dinner!) on Friday night, he can't argue with the fact that he _made_  money by doing practically nothing. Talked a lot, mostly. Which he usually does for free...

Anyway, it's a pretty easy decision to make come Saturday morning to just stay in San Francisco and see where this hooker thing takes him. He wallows in the bed in the (free!) hotel until it's time to vacate, then he spends most of the day driving and walking around town, taking in the sights and window-shopping. Really, it's a pretty awesome way to spend a Saturday.

Stiles still has the free food that Frank loaded him up with, so he eats that, not wanting to spend any of his $300. He has to get home, and while he has plenty for gas, he has an electricity bill to pay. (The leftover $275 after he fills up his tank won’t quite cover all of the bill, but it’ll take a huge chunk out of it.) That, and the water bill _and_  the mortgage are coming up soon. Oh god, and the internet and cable bill.

So it's well after dark, around 9 at night, and Stiles is right back in his little corner, hanging around and trying to look sexy. And maybe it's just him, but there seems to be _way_  more foot traffic tonight than last night.

It isn't too long before he's picked up again. By a nice-looking guy in his mid-forties going by the name of Rick.

Who, much like last night, talks to him for about an hour, pays him $150, and goes on his way. Stiles is still a virgin.

And the next trick--Casey--is the same. And the next, and the next.

By the time Sunday morning rolls around--Stiles getting _another_  (if slightly less extravagant) hotel room paid for on his behalf--Stiles is up almost _two fucking grand_  and still in possession of his virginity. Hell, he hasn't even been kissed (unless you count the practice kisses he traded with Scott in the fifth grade, which he doesn't, and neither should anyone else). He _also_  has a new-to-him hoodie, thanks to Nick who "thought he looked cold." It's lined with fleece and very, very warm.

Stiles drives home to Beacon Hills feeling rich and more than a little confused.

\--

Every day, after school, Stiles visits his dad in the hospital. He doesn't bring up what he did this weekend (he's not an _idiot)_  and they don't talk much about the bills and the payments anyway. His dad is tired and gray and sick-looking, and Stiles wants to cry every time he sees him.

Which is why, next weekend, he goes right back down to San Francisco. He was able to pay his utility bills in full and fill up his pantry with food at home, with money left over besides, tucked away for the impending mortgage payment. He's got a bag with snacks and his new (Thanks Nick!) hoodie to help keep off the chill of the nights and a couple of extra t-shirts, small, that stretch tightly across his chest and shoulders and barely touch the hem of his jeans when he's standing straight and still. Oh! And he bought a stick of eyeliner because he saw a movie poster with Channing Tatum on Thursday who was wearing eyeliner and _boy howdy_  Stiles is going to try to make himself look as sexy as him. Well, it may be asking a bit much of the little stick of eyeliner, but Stiles is going to _try._ Because goddamn it, Stiles is determined to get paid for his virginity if it kills him.

He waits around in a new corner he found, slightly closer to the clubs. He doesn't have to wait long.

Three hours and four johns later, Stiles is $600 richer and no closer to being de-virginized. His sob story about his dad being in the hospital and his mom being dead is less emotionally wrought than it is recited by rote. By the end of the night, he's collected another $245 and is the proud new owner of a full first aid kit, three dozen condoms, a bottle of lube, and a gift card to Applebee’s.

By the end of the weekend, his stash includes two new pairs of shoes, a pair of jeans (Thanks Stacy!), four new shirts, and a Mets baseball cap. He has almost $2300, his virginity, and a near palpable desperation to get laid 

\--

When his dad asks Stiles on Monday what he did that weekend, Stiles tells him, "I hung out with some new friends I made." 

His dad nods, proud of how social his son is becoming. Stiles just pats his dad's hand and thinks that he can probably afford to go organic when his dad finally gets released from the hospital tomorrow morning.

Three weeks pass by, and every weekend Stiles makes an excuse to go down to San Francisco to try to sell his virginity. Each Sunday, he returns to Beacon Hills, laden with gifts and money and no closer to losing his virginity than he was that first Friday night. Steve does kiss him on the cheek, though, last Saturday, after Stiles calls him slightly in a panic because one of his tricks wanted him to move in with him. Only, when Steve comes to rescue him, he starts to make--albeit less creepy than Jonas's overtures--proposals of Stiles moving in with him and Adam. Stiles steadily declines, and Steve just gives him one big honking kiss on the cheek, hugs him, and wishes him well.

Stiles starts to consider moving in with the first person that offers him a blow job. Or tells him to give them a blow job. Whichever. Stiles isn't picky.

Stiles has managed to sneakily pay off the mortgage for the next three months, has covered the yearly deductible for his dad's medical bills, and has started a pretty nice emergency fund--just in case. He has watches and books and clothes and more condoms and lubes than he thinks he'll ever be able to use in a lifetime, what with his ever-present virginity and all.

He's standing by his corner near the clubs, playing on his new phone and watching the people walk by and give him odd, sometimes sympathetic looks. He nods at them, smiling distractedly. Scott is complaining about Allison and Stiles systematically sends him emoticons to punctuate Scott's girl troubles when a very familiar voice grumbles very, very close to him.

"Stiles."

Stiles looks up, startled, into the very familiar, very green eyes of Derek fucking Hale. He swallows hard. "Hey Derek. What are you doing here?"

Derek frowns. "I could ask you the same thing."

Stiles opens his mouth, but doesn't really know what to say. If he tells Derek that he's attempting to turn tricks--less because his dad is in the hospital and more because _he is so fucking done with being a virgin he just can't anymore--_ there's a chance that Derek will tell someone who will tell Dad. And then Stiles will be murdered. By his father. Or one of his deputies, more likely.

But he doesn't really know how else to answer what he's doing by the gay clubs in San Francisco dressed as a hooker so... oh. Wait. He does. "I'm, uh, clubbing."

"Dressed like that?"

Stiles looks down at himself. He's wearing tight black jeans and a very, very tight t-shirt with strategic rips in the abs and chest. One of his nipples is poking out. The left one. The one he likes. "Yeah?" he answers slowly.

Derek cocks an eyebrow at him. "You look like a hooker."

Stiles laughs. "Funny that you should say that."

Derek glowers at him. Stiles sighs. "Don't tell my dad."

Both of Derek's eyebrows shoot right up into his hairline. Stiles texts one more little sad face at Scott, then pockets his phone. "Look, there's a really good diner just a couple of blocks from here." He hooks his thumb over his shoulder, indicating the way. Derek shrugs, and follows as Stiles walks to his favorite restaurant.

They're seated by Cindy, who immediately greets Stiles with a hug and a, "How are you doing, sweetie?"

Stiles smiles broadly, readjusting his shirt so his nipples are fully covered. Cindy is old enough to be his grandma. He doesn't want this grandma seeing his nipples. "Pretty good. It's a lot warmer than last week."

Cindy tuts and pats Stiles on the cheek and shoos both him and Derek to Stiles's booth at the back. Stiles flops into his seat, and looks at Derek, who more gingerly sits down, looking behind him.

"What was that?"

" _That_ was Cindy and she is a lovely woman and you'd better be nice to her or I'll call Steve." Stiles finishes this threat just as Cindy walks back up to the table with Stiles's Dr. Pepper and a water for Derek. Stiles takes his drink and beams up at Cindy. "Thank you Cindy."

"You're welcome darling. Just wave when you're ready to order." Cindy drops a menu in front of Derek, spins on her heel, and walks away. Stiles turns back to Derek.

Derek looks poleaxed.

"Cindy's the best," Stiles tells him. Derek nods slowly.

While Derek is looking over the menu, Stiles drinks his soda and talks. "So, my dad was in the hospital."

"I heard." 

"And there are lots of medical bills."

Derek just raises an eyebrow.

Stiles powers on. "And there's the house payment and utility bills and stuff like food. He's had some sick leave but that was pretty quickly eaten through." Stiles shrugs. He's deviating from his normal sob story script, but that's to be expected. It's Derek. Derek is always making Stiles deviate from script. "I didn't know what else to do."

"So you came down to San Francisco to be a prostitute."

Stiles takes a long slurp of his drink, staring Derek straight in the eyes. Derek stares back.

"Yeah," Stiles answers.

Derek rolls his eyes so hard Stiles thinks he can hear them. "That is the stupidest thing I've ever heard."

Stiles sets down his drink. "Statements like that enforce the negative stereotypes that make sex work and the people that engage in it a living hell." Derek blinks at him. More softly, Stiles follows up with, "Just so you know."

There is a long moment of silence. Stiles waves Cindy over, and they place their orders. Stiles orders more curly fries, because one can never have too many curly fries. Or they can--actually that's why his dad was in the hospital in the first place--and therefore Stiles has placed a six-month moratorium on curly fries in his household. He can only get them on weekends, miles and miles away from his father.

After Cindy walks away again, Stiles looks at Derek and says, "I'm assuming you're paying for the meal."

"Is this how you treat all your clients?" Derek is back to the eyebrow-raising sass.

Stiles bursts out laughing.

Derek shoots him another look like Stiles has lost his ever-loving mind. And perhaps Stiles has, because that is _the funniest thing he has ever heard._

"Dude, dude. I can't. I can't even." Stiles sucks in just enough air that he is able to calm down without passing out. "There are so many hilarious levels of irony in that statement."

Derek is still looking at Stiles like he has lost his ever-loving mind.

So Stiles explains it to him. "First, can I call them clients when none of them have actually had sex with me?"

"You haven't had sex with them?"

Stiles shakes his head. "No. And god, I have been trying. So hard. Like, really, really hard with the trying to have sex."

Derek narrows his eyes and looks at Stiles. "Is it an," he darts his eyes around the room and whispers, "an equipment problem?" 

Stiles wads up a napkin and throws it into Derek's face. "No!" More calmly, he answers, "It's a ‘They Don't Want to Have Sex With Me, Just Give Me Nice Stuff and Money’ problem."

Derek's face is so blank Stiles could draw a picture on it.

"For reals," Stiles reiterates.

"They don't want to have sex with you, just give your nice stuff and money?" Derek repeats finally.

Stiles sighs. "Yeah. It's all 'poor baby, are you cold? Are you hungry? Call me if you're in trouble, you're not alone, life will get better.’ Blah blah blah."

Derek actually snorts with laughter. "They want to take care of you?"

"I knoooow." Stiles falls onto the table, melodramatic in his desperation. "I'm going to be a virgin _forever_."

Derek makes a noise like the universe is personally out to get him. He reaches into his pocket and out his wallet. "How much?"

"For what? Dinner? You'll have to ask Cindy--"

Derek growls and slaps a twenty on the table. "For a _blow job_."

Stiles looks at the bill, dumbstruck. He hadn't quite gotten to the "figuring out his rates" part of the business--what with the people never actually wanting to have sex with him. He thought back to the only prostitute he was familiar with: Vivian Ward from _Pretty Woman._

"$50."

"Are you serious?"

Stiles leans back in his seat, lacing his fingers behind his head. "$50. Take it or leave it."

Derek growls again and slaps a few more bills down on the table. "Fine. You got a place, or..."

Stiles startles forward. "Wait, are you serious?"

Derek raises his eyebrow at him, smirking. Stiles jaw falls of its own accord. But he recovers quickly, grabs the money, and waves at Cindy, who trots forward, their check and boxed-up food already in hand. "Pay the lady," Stiles says, and stands up from his seat. Derek grumbles, but pays her, too.

Stiles leads Derek to his hotel room this weekend (Thanks Oliver!), several blocks away from the diner. It's a long but good walk. Derek hovers next to Stiles, arm brushing his every so often. Stiles finds himself weirdly grateful for his warm presence.

Stiles lets Derek into his room with a flourish. "Mi casa es su casa."

"Gracias."

Derek looks around the room. It's pretty nice--good shower, comfy bed freshly made by the maids earlier this afternoon, decent television. Stiles walks over to the bed and sits at the edge. "Alright, come on. Let's get this party started."

"Maybe you'd get laid more if you didn't refer to it as 'a party,'" Derek suggests.

Stiles rolls his eyes, but pats the edge of the bed anyway. "Just come over here."

Derek stalks closer to Stiles, a slink in his step that makes Stiles's mouth water and his pants tighten. Stiles leans back on his hands, staring up at the predatory look on Derek’s face. It’s a good look.

"Take off you pants." Derek practically purrs.

"Um." Stiles must have heard Derek wrong. Isn't Derek supposed to be one dropping trou’? 

Derek gets right up into Stiles's personally space, standing in between the vee of Stiles’s legs. "I'm going to blow you. Take off your pants."

"You paid me. Aren't I supposed to be blowing you?"

Derek drops to his knees and Stiles nearly has a spasm right then and there. "Take off your pants, Stiles."

Stiles nods vigorously and hops up just enough to shimmy out of his jeans. When they're down to his knees, Derek reaches up and hooks his fingers in the waistband of Stiles's boxers. Stiles manages to stay standing just long enough for Derek to slip his underwear down. When his cock is free, Stiles falls back onto the bed.

Derek leans forward to dart a quick lick to the underside of Stiles's shaft. "I can't believe you're still a virgin."

"I swear to god if you don't put my cock in your mouth I'm going to bash your head in."

"Ah. Starting to figure out why."

Stiles grabs Derek's hair, frustrated beyond belief, but Derek just laughs. He leans in and swallows Stiles whole. Derek's mouth is amazing--hot and wet and Derek is sucking just hard enough for there to be suction. Stiles doesn't have anything to compare the experience to, but he's pretty sure that Derek is going to be in the top ten sexual encounters for the rest of his life. Derek tongues the underside of Stiles's head and does this hard suck move and Stiles collapses back on the bed. Derek just moves with him, like a sexy fellatio leech.

Wow, you really can lose brain cells during good sex.

Derek pets the inside of Stiles's thighs, easing up to play with his balls. His lips and tongue make loud, raunchy smacking noises, joining Stiles gasping and moaning. Distantly Stiles thinks that this room finally sounds like it's rented to a hooker. He giggles a bit.

Derek pulls off just long enough to give Stiles a questioning eyebrow. Stiles just waves his hand at him. "I'm a real hooker now. I'm excited."

Derek snorts in amusement and dives back down, mouth first.

It doesn't take very long, what with Stiles being a virgin and all (although, not anymore! Thanks Derek!), before white sparks behind Stiles's eyelids and his pleasure crests and he comes, spilling down Derek's throat. Derek swallows like a pro.

Stiles is breathing heavily, staring at the ceiling, and Derek crawls onto the bed up next to Stiles. They look at each other for a moment, just grinning at each other.

"Hi." Stiles is a bit loopy in his post-orgasmic bliss.

"Hi," Derek returns.

"That was awesome."

Derek reaches a finger into the carefully made slit in Stiles's shirt, tugging at the hole until his nipples are exposed to the air. He plays with them, pads of his fingers brushing lightly over nubs. Stiles's dick makes a tired jerk of interest, and Stiles moans.

"Ugh." He bats Derek's hand away. "Too sensitive." 

"Give it a minute."

Stiles laughs, looking up at Derek's face. He has really pretty eyes. Long lashes. Great cheekbones. Stiles reaches up and touched Derek's cheek, petting it lightly.

"Think you're up to letting me try that?" Stiles asks, voice soft.

"Do I have to pay you?"

Stiles flips Derek's nose. Derek playfully tries to bite him in retaliation. "No," Stiles says and laughs.

They lay on the bed for a few long moments, getting their breath back. Well, Stiles wrestles with his breathing, Derek mostly just lounges like an overgrown cat. Finally, when Stiles is breathing relatively normally again, Derek lifts his hips and undoes his pants enough to push them down his hips. Stiles laughs and rolls over on top of him. He's reaching for Derek's hips when Derek grabs his face, palming his cheek with one hand. Derek leans up and kisses Stiles. His stubble is kind of prickly but his lips are soft and he kind of tastes like salt--Stiles realizes he’s tasting himself, and he moans.

Not bad for a first kiss. In fact, it’s really, really nice. Stiles chases after Derek’s lips and manages to get a few more first kisses, savoring the way Derek feels against his mouth.

Derek releases him after a moment and gives him a shove on the shoulder. "Get to work, ho."

Stiles punches Derek in the shoulder. Derek just laughs.

He wiggles his way down Derek's body until he's at eye level with Derek's cock. It's large and uncut, but not like, monster dick huge like in some of the porn videos Stiles has watched. It smells musky.

Derek smirks down at Stiles. "Like what you see?"

Stiles just opens his mouth and sticks Derek's cock in his mouth. He sucks on the head, just tasting it. It tastes a bit like skin, but heavier, the texture velvety smooth against his tongue. Stiles moans around Derek's cock, and Derek grunts above him in pleasure.

Stiles has no idea what he's doing so he tries to make up for it with enthusiasm. He tastes all along the head and shaft, playing with the slit, trying all the things he thinks would feel good. It seems to be working, at any rate, with Derek's increasing noisiness urging him on.

He thinks he has a good rhythm going when Derek puts his hand on his head. Stiles looks up at him through his lashes, and Derek groans loudly.

"A bit harder," Derek instructs, and Stiles readjusts his grip.

Stiles's jaw is just starting to ache when Derek starts making weird huffing noises above him and his hips start stuttering and losing pace. Derek’s hands grip the back of Stiles head, like he wants to push Stiles's head down but he’s stopping himself. Stiles figures now is not the best time to stop. He keeps his head down and keeps sucking and working Derek's shaft.

Derek gives a little cough of warning before he's coming down Stiles's throat. Stiles pulls back a bit--not startled per se, but not expecting the salty flood of come either. It's thick and warm but not hot like he expects. It leaves a salty, slippery taste in his mouth after he swallows.

He leaves Derek's cock alone and looks up at him. Derek is breathing heavily, eyes wide in amazement, staring at Stiles. Stiles just grins.

"Good?"

Derek nods, mute. Stiles crawls back up Derek's body and flops down beside him.

"I'm not a virgin anymore."

"Please don't start singing," Derek huffs between breaths. Stiles bites him on the shoulder and Derek laughs.

They doze off for a bit, just enjoying each other's physical company. When they wake, they make out for a long time in between arguments about virginity loss ("It's a social construct." "I still want to do it in the butt." "You're a butt.") and other important topics, like if mushrooms as a pizza topping are grounds for insanity.

They stay in bed for the rest of the weekend, and Stiles steadily works his way down his sexual bucket list. Derek has to stop by an ATM twice.

When they both return to Beacon Hills, they part ways at Derek's apartment. Stiles walks Derek to his front door and kisses him goodbye, like it was a date. Derek just grins into Stiles's mouth.

"Call me."

"I will," Stiles promises.

Stiles drives to his house, where his father is waiting for him on the front porch, sheets of paper in hand. Ah crap. Stiles shuts off the engine of his Jeep and silently offers gratitude to his foresight of wearing semi-normal looking clothing for the drive back up home. He gets out without having to hide his nipples or anything.

"Have a good weekend, Stiles?" his dad asks. His voice is just this side of hard and disapproving. Stiles swallows heavily.

He grins innocently, or at least, as innocently as he can manage. "What's up, daddy-o?" 

His father waves the sheets of paper in his face. "Wanna tell me how my 17-year-old son has managed to pay three months of mortgage payments, not to mention the other bills _and_ $1500 of my medical expenses?"

Stiles bites his lip and wrings his hands together. "Um, no?"

"Stiles."

"Can we drop it? I'm not hurt and it, um, mostly wasn't illegal and if I delve into more detail it may literally give you another heart attack, so--"

"Stiles!"

Stiles cuts off any further protest by hugging his father hard. "I'll do anything for you, Dad, you know that?"

His dad clutches Stiles just as tightly. "I know, kid. I just wish that whatever you did it was on my side of the law."

Stiles pulls back. "It was! Mostly. Honest to god, that's the truth!" 

"Uh huh." 

Stiles pats his dad's shoulder and tries to hide his wince. "So, what's for dinner? No, wait, don't tell me. I'll get something started. How about pasta and salad? I've got organic whole wheat rigatoni and this pretty rad pasta sauce--"

"Stiles--"

Stiles hurries into the house, trying to outrun his father's protests. "It's for your own good, Dad!"

"Stiles!"

\-- 

Stiles's life is pretty much back to normal after that. He doesn't go down to San Francisco every weekend any more. He plays video games with Scott (who has _incessant questions_ for two weeks straight about Stiles's time as a prostitute) and goes on dates with Derek. He and Derek do the do in several different positions and Stiles is really fucking happy.

He still calls Steve sometimes, because Steve is awesome and gives really good advice. And Adam gives hilariously bad advice which is, in itself, kind of its own advice. Anyway, Stiles calls them a lot.

His dad finds his stash of strategically revealing clothing, and they both solemnly vow never to speak of it. Still, though, Stiles catches him looking at the bills in amazement and staring at Stiles from halfway across the room.

Sometimes, though, Stiles will go through that stash of clothing, pull out an outfit, and take a trip down to San Fran. He mostly goes clubbing instead of hanging out on street corners, but inevitably someone will pick him and pay for his dinner and buy him pretty things and tell him that "he's going to make it," and to "just stay strong."

And sometimes, when he's down there, Derek will find him, shove $50 or $100 into his pocket, and drag him by his belt loops to the nearest bathroom to do something incredibly dirty to his body.

Stiles can't decide which one of those events he likes better.

END

**Author's Note:**

> Thank you to the lovely [mikkimouse](http://archiveofourown.org/users/mikkimouse/profile) for being the adorable sweetheart she is and betaing this for me. Also for putting up with me emailing her random tidbits of story going LOOK LOOK AT WHAT I DID and humoring me so graciously. I LOVE YOU BB.
> 
> Come find me on [Tumblr](http://domesticated-chaos.tumblr.com) and [Twitter](https://twitter.com/ErisOReilly)!


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